I’ve been thinking a lot lately about how uncomfortable we’ve become with not knowing.

Not just personally… culturally… institutionally… professionally. Somewhere along the way, uncertainty stopped feeling like a normal part of life and started feeling like a system failure. Something to eliminate… something to optimize away… and maybe no force accelerated that shift more than the internet itself (and the treasure trove of data it provided). This week on Thinking With Mitch Joel, I had a conversation with Simone Stolzoff, who recently published the book, How to Not Know – The Value Of Uncertainty In A World That Demands Answers. Simone’s work circles around our increasingly fragile relationship with ambiguity, and the more I sat with his words, the more I started wondering if the internet didn’t actually make us smarter… maybe it just made us less comfortable sitting with uncertainty?

Because before the internet, uncertainty was everywhere.

You didn’t know the answer immediately. You had to sit with the question. You argued about things at dinner without instantly fact-checking them. You started businesses without perfect market validation. You made career decisions without infinite LinkedIn threads, YouTube explainers, Glassdoor reviews and Substack commentary from “thought leaders” who somehow seem absolutely certain about everything all the time.

Now… our expectation is instant resolution or, worse, instant reassurance (when was the last time you waited for your favorite song to play on the radio?).

Every question has an answer. Every decision is backed by data. Every strategy is validated before it launches. Every risk is modeled, measured and reduced before anyone takes action. And while that sounds smart (and sometimes is)… it has also quietly changed how we think. Or worse… how little we’re willing to think without reassurance. Companies today are drowning in dashboards, analytics, consumer insights, heat maps, attribution models and predictive systems. We have more information than any generation of leaders in history. And yet, oddly, organizations often feel more risk-averse, slower and less imaginative than ever before.

Because a lot of data today isn’t being used to explore possibility and unlock imagination… it’s being used as insurance.

Insurance against being wrong… against accountability… against discomfort. What’s the old B2B saying: “no one ever got fired for buying IBM”… well, now you can replace IBM with data. And that changes how organizations behave. Many of the biggest business breakthroughs in history happened long before leaders had this mass of analytics available to them. They made uncomfortable bets. They trusted instinct. They moved before the spreadsheet could fully justify the move. They listened to the people they hired (not just the spreadsheets those people provided). Today, many organizations seem trapped in an endless loop of optimization… improving what already exists because truly new ideas rarely arrive with clean data attached to them. And if you look closely, many of the biggest companies today aren’t really inventing new categories… they’re refining existing ones with more precision, more efficiency and less risk.

Once a culture becomes addicted to certainty, imagination starts to look irresponsible.

When every decision requires validation, we slowly lose our tolerance for ambiguity. And ambiguity is where creativity lives. It’s where invention lives. It’s where original thinking usually begins. The internet gave us infinite access to information but it also trained us to believe that uncertainty itself is unacceptable. Now AI is amplifying this even further. Why wrestle with complexity when a machine can summarize it? Why sit with the tension of a hard question when an answer engine can generate a confident response instantly? The danger isn’t that the answers are always wrong (I’m not on the “don’t use AI because it hallucinates” train). The danger is that we stop developing the emotional muscles required to live without immediate certainty.

Because life doesn’t actually work that way.

Leadership doesn’t work that way… creativity doesn’t work that way… relationships definitely don’t work that way. And maybe that’s the real skill we should all be working on right now… not knowing everything. But becoming comfortable enough with uncertainty that you can still move, decide, build and imagine… before the answer fully reveals itself.

What do you think? Are we using all of this information to make braver decisions… or just to protect ourselves from making any real decision at all?

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